Task Management and Prioritization

Last week, I shared the opener to an ongoing series of blog posts on an important topic to me: Attention Deficit Disorder. (That first post really focused on sharing my story, which was important to me for a number of reasons.) I wrote about my motivations, which include sharing what’s worked for me in dealing with my own journey with ADD, particularly in a business setting.

This really kicks off that effort. I’ll begin with the thing that’s been hardest for me forever: task management and prioritization.

This is hard for everyone. For someone with ADD, though, it can be crippling. Together, deciding what needs to get done, when to do it and who should be responsible form the single most important element of my ADD management. And, while I’m writing from my own point of view, I hope this content can be helpful to anyone dealing with a complicated and busy work environment. (So even if you don’t lose your keys every morning or need constant reminding to take your dry cleaning in, you should totally still read this.)

By design, WorkBook6 is vulnerable to distraction. We represent the interests of dozens of companies. These companies pay us to keep them moving forward, and there’s always important work to be done. Deciding which tasks to take on, and for whom, is informed by a fluid field of context. As you might expect, keeping this all straight requires near-constant stewardship and sound decision-making. The process involves extensive communication with our team, our clients and our prospects.

Over time, I’ve come to understand what works best for me and establish a format that helps me to maintain progress across all facets of the business. My system is neither elegant nor complicated – with so many agendas in play, and with each having plenty of subtasks, I’ve learned that maintaining forward momentum demands simplicity. My task management strategy is thus, like, super-straightforward.

Before I do anything else, I run all new tasks through the same four questions:

  1. Should I (or we) do this at all? If this sounds simple, I’d challenge you to look back on the last 30 days of your own activity. Did you commit time and resources (either yours or your team’s) to tasks that didn’t have a measurably positive impact? What did you learn from that?
  2. What type of task is this? Is it revenue-impacting? Is it operational? Personal?
  3. Does this need to happen now, or later? Sound obvious? It’s not. Again, look back on the last 30 days. Have you committed yours or your team’s time to the completion of a task that, while useful, wasn’t timely? Did you do things prematurely? Again, what can you take from that experience?
  4. Should I do this myself, or would someone else be better? This one speaks to effective management. I’m frequently guilty of taking on too much, myself. Asking this question helps me recruit resources. My logic is simple: will this move forward more efficiently in my hands, or someone else’s? If it’s important that it gets done, the single most respectful thing I can do is be honest about who should carry it forward.

Once I’ve run my tasks through these questions, I put them where I can clearly see them, and organize them based on the conclusions I’ve drawn for them. My process is as follows:

  1. I write each task down on a post-it note (I prefer the Miami Collection from Post-It in 4” x 4”). I separate these by task type. Revenue-impacting tasks are written down on a green note; operational matters are always orange. Personal gets yellow.
  2. Next, I make two preliminary piles: one for the stuff that doesn’t need to happen right away and another for those tasks which demand immediate attention.
  3. I then separate each pile into two smaller ones (so I end up with four): one pile is for tasks that are best handled by someone else; the other is for tasks I’ll take personal accountability for completing.
  4. I stick the tasks on a four-quadrant grid which takes up on the southern wall of my office. This is my ‘big board.’ ‘Now’ and ‘Not Now’ form the x-axis; the y-axis contains the labels ‘Me’ and ‘Not Me’. To the left, I keep a little ‘Done’ pile. (This is recent – I used to throw the finished tasks away, but seeing a pile of completed tasks makes me feel good.) The whole setup ends up looking like this:

I follow some simple rules for distribution. I know that if I take on too much, personally, the system breaks down. So, the ‘Me’ tasks should never make up more than half of what the ‘Not Me’ ones. My thinking around timing is similar. If I try to do everything right now, the effect is the opposite – nothing gets done. So, I never let the ‘Now’ tasks make up more than half of the ‘Not Now’ items. This system allows me to make progress on what’s most urgent, and then re-prioritize items as I work through the backlog.

Another thing I’ve learned: when transparent, this process doesn’t only help me – it also provides a venue for building consensus. I practice transparency around this entire system, both internally and externally. I’m honest with our team and I ask for their guidance. I do the same with our clients. I ask them to help me prioritize the tasks we’re discussing. If a client sees a particular partnership as being critical, now, I agree to make that a priority. If I don’t think I’m the right person to complete the task, I share this as well. And if I get pushback on this, we discuss it openly. Sometimes I’m wrong. Other times, the instinct to delegate/collaborate is the right move. In either case, I’m grateful for the opportunity to land on the right direction, together.

This is my system. It’s not foolproof, but I’ve found that it works really well for me. Process wonks may view this as entirely too elementary. Many will point out that their business is way too complicated to fit into four quadrants, or that ‘not now’ is far too general a characterization. Right on, folks – do you. I’m half-crazy and what I do is not for everyone. But if you’re feeling overwhelmed, or scattered, you might want to try this out for a few weeks. If you do try this, let me know how it works out. I’d love to hear from you.

Thanks as always for reading. I hope this helps some folks!

Strategic Partnership Workshop – Full Speaker Announcement!

With InsureTech Connect now just a couple short weeks away, it feels timely to share more details on what we’re planning with our Strategic Partnership Workshop. At this point, our schedule and agenda are finalized, and I’m very happy with where we’ve landed. Attendees will hear from a talented and diverse group of thought leaders whose businesses touch the insurtech ecosystem in a variety of interesting ways. You can access the full agenda, here, but I’ve written a bit about each of our sessions, below:

We’ll begin with a discussion about growing profitably with a disruptive model – this discussion will feature senior executives from two insurance marketplace businesses: Abby Reddy from Quotacy and Marc Buro from InsuraMatch (part of the Plymouth Rock Assurance Company). I expect this session to be wonderfully informative for anyone working to solve for consumer choice and reduce friction in their customer acquisition funnel.

Next, we’re going to focus on insurance-adjacency and the potential this holds for improving customer acquisition, retention, and profitability. Daniel Weaver from Updater’s insurance division will speak to the ways insurance marketers can leverage high value audiences with a stated need for coverage. Chad Lovell from Cross Country Home Services (and formerly an executive with Liberty Mutual) will share important insights on the adjacency of home services to home insurance – and how a data and technology driven partnership within the connected home space can reduce claims and mitigate losses.

Because we believe that partnerships are central to the creation of enterprise value, it seemed logical to focus content on this. So our third and fourth sessions will do just that.

We’ll begin the perspective of founders whose partnership successes ultimately led to their acquisition. Brian Ocheltree from LeadCloud (acquired this year by National General Insurance) and Hal Schwartz from Quilt (also acquired this year by Mass Mutual) will help us all better understand the path to acquisition for a partnership-minded insurtech business. This will be a fantastic session for anyone leading or contributing to a startup, or folks who want to better partner with innovative new businesses.

Finally, we’ll look at partnership within this space from the investor’s perspective. This session – our last of the day, is designed to help us all better understand how capital views businesses which go to market through partnership. We’ll have two very unique perspectives to learn from: Grace Vandecruze, whose firm advises large insurance enterprises with regard to mergers and acquisitions, and Ashish Dudani, who runs an early-stage fund which invests in new insurance ventures.

But wait, there’s more! (I’ve been hoping to say/write this for a while – thanks for indulging me.) We’re delighted to welcome members of Gamma Iota Sigma, the nation’s largest fraternal organization serving students who plan to enter the insurance industry. These students are all part of a scholarship program announced earlier this year. We’ll even get to hear from the organization’s CEO, Noelle Codispot.

Seriously, folks, we’ve been working hard to bring forward a great agenda. As you can see, there’s a lot of content planned – and we’re going to deliver it all within a four-hour window. As a refresher, below are the details on this event:

Monday, October 1
1:00 – 5:00 PM
MGM Grand Rooms 203 and 204

If you haven’t yet registered for InsureTech Connect, you can do that, here.

If you have, but haven’t planned out the pre-day activities, I’d love for you to join us!

See you in Vegas! 

ADD – My Story

Like many in my field, I deal with Attention Deficit Disorder. Every day. Since second grade, when my parents and I sat in the principal’s office at my elementary school and were told that I’d be soon transferred into the special education program. (I’ll revisit this, later in this post.)

You may wonder why I would share this. Four reasons, really:

  1. I value vulnerability and there’s no shame in talking about mental health. ADD is core to who I am – why not discuss?
  2. I want to help people who, like me, live on the margins of ‘normal.’ I run a business. I help lead a family. I volunteer whenever I can. Just like everyone else, I figure out how to make it all work, but I do it while carrying a story that involves the word ‘disorder.’
  3. I believe that when properly channeled and supported, ADD is my super power. I may struggle to read my mail, remember my car keys in the morning, and keep my inbox at zero, but I also get to see things other, more organized people might miss.
  4. I want to share what works for me. And I want to hear from others what works for them. More specifically, I want to create content that covers how people in business can operate at an excellent level in a business environment while staying true to who we are as people.

Mostly, though, I just want to tell you my story.

Let’s go back to that meeting in the principal’s office. Old school. Fake wood paneling. Musty air from the swamp cooler. Citing the observation that I couldn’t read, my teacher and the principal sat with us and delivered the news that I was to be moved into the ‘portables’ – a collection of prefabricated buildings offset from the school where the special education program was housed.

My parents were blown away. I was actually an avid reader. My dad stood up, drove home (we lived a block away) and returned with one of my favorite fishing magazines.  I read from it for the group. Blank stares. Awkward silence. A bit of hand-wringing. In the end, their decision stood – if I was to remain at the school, I would do so within the confines of the special education program.

My folks pulled me out of the school, and enrolled me into a new, private school in the area. The Awakening Seed School featured small class sizes, a social learning environment. Best of all, they let kids’ passions inform their assignments. It was magnificently different. The founders – family friends to this day – were total hippies. We planted gardens and discussed global warming (well before it was a commonly discussed thing). I flourished.

We also visited a child psychologist, and then a psychiatrist. I was officially diagnosed and prescribed a new drug called Ritalin. I had officially become one of those ‘different kids.’

A.D.D. has been a dominant theme in my story ever since. I’m still haunted by the all-nighter with my parents the evening before report cards were to be sent home in sixth grade (I had turned in exactly zero assignments). Sports weren’t an outlet, yet, either – I’ll never forget the embarrassment of tackling my own team’s quarterback on the freshman football squad. And we still laugh about the look of shock on my parents faces when I brought home a far better than expected SAT score, despite my mediocre GPA at the one of the city’s lowest performing high schools. College presented new challenges, but also allowed for new successes. Work, as well. At each life stage, I’ve learned to leverage the unique tools that ADD provides me, and I’ve looked for support in the many areas where I’ve needed help.

I’ve also come to understand that at least in my case, this will never really go away. For me, that’s been more good than bad.

Thank you for reading this. In the future, I’ll be much, much more focused (ha!) about how I function with ADD in a business setting. I’ll cover organization, task management, stress reduction, team dynamics and likely much more. But first, I wanted to tell you my story.

Breaking Through (Part Two): A Roadmap to More Effective (and, respectful) Prospect Engagement

Last week, I wrote about a somewhat humbling lesson I learned about being open to inbound sales and business development communication. You can read that, here, but I’ll quickly summarize it for you:

  1. I made a snarky, sarcastic post on LinkedIn about cold outreach messages.
  2. It got an unexpectedly high response rate.
  3. While many agreed with my snark, some other folks suggested that I was misguided.
  4. I wondered if they were right.
  5. They were, at least a little.
  6. Lesson learned.
  7. I still think there’s a better way.

So, in an effort to right my own wrongs, I decided to share some outreach and communication practices that have served me well in my own career. Are they the best, ever? Probably not. But over the years, I’ve learned what works for me, so that’s what I’ll share. My goal is that this can be decent reference material for anyone who’s struggling to break through the noise and make a connection. (In this sense, I hope our readers will share this content so that others might see it.)

 Staging is Really, Really Important

I think about sales and business development communication as fitting into distinct segments within the decision-making cycle. I can get pretty granular with this stuff, but I’ll keep it simple, here, and boil it down to three segments. The first is preliminary engagement, the second is discovery and the third is commercialization. If you work backwards from the goal, this is pretty linear:

  1. if you hope to form a commercial relationship with someone (ie: sell something),
  2. you must first understand them; to do that, you’ve got to create a dialogue,
  3. which means you’ve got to get them on the phone (or get a meeting).

 I’ve organized my thoughts in these categories, below:

 Stage One: Preliminary Engagement

This is really the most critical stage in my opinion. An analogist might think to compare this to the snap of a football, a plane taking off or the foundation for a house. The point is: without a clean beginning, everything else will be more likely to fail. Drawing on personal experience, I can point to countless awkward business discussions that could have been improved with a cleaner introduction. And because I think this process’s only deliverable goal is to facilitate a 1:1 dialogue, being messy at the start is unacceptable. Here are some things I always strive for in early stage discussions:

  1. Assume that your prospect is really, really busy. Then, stop assuming. By this, I mean that before you can develop empathy for your prospect (which is, like, critical to selling stuff), you must first secure the opportunity to develop it. And this means you have to find a way for them to process your outreach and agree to talk to you. If you assume that they’re very, very busy, and that your message is going to fit awkwardly into an already over-loaded day, you’re probably right. So, choose your words wisely.
  2. Be respectful and acknowledge what’s going on, here. Tell them that you’re trying to determine your value to them, that you’ve got a hunch you could be helpful. But, that you’ve got to learn more to know for sure.
  3. Keep it very simple and brief. A good rule of thumb is to give yourself a maximum of five sentences: one to introduce yourself, two to describe your product or service, one to present your goal and one to secure the next step.
  4. Don’t sell anything. Seriously. This is why some people can’t stand some salespeople – bad ones try to sell stuff without any thought or empathy for their prospect’s need. You’re not there yet – the best deal you’re going to close right now is a discussion.
  5. End with a yes/no question. State and serve your purpose. Say something like “I’d really like to better understand you/your business/your company – with a goal of seeing if we’re a fit for you. Would you be open to spending a few minutes with me on the phone to do this?”

Stage Two: Discovery

If we’ve done our job in the preliminary stage, we’re on to our first 1:1 engagement with our counterpart. With a prospect on the line, I think it’s really important that this stage lead to an understanding the potential for this new relationship. This should be focused on education – for both parties. Below are some things I’ve found helpful in my own career when I’m in the discovery phase:

  1. Maintain the respect you established in the introduction, as well as the candor. I like to begin the discussion with a straightforward and simple statement of my goal. “I want to learn enough today to know whether we’re a good fit for one another, and I want to make sure you get to do the same.”
  2. Suggest a specific format, but defer to your counterpart on who goes first.
  3. When it’s your turn, be brief and clear.
  4. When it’s their turn, ask great, simple questions that help further the education.
  5. Whatever you think you’ve learned, restate it and ask for confirmation that you’ve got it right.
  6. If you think it’s a fit, let the other party know what you’re thinking at a high level, and then ask if you’re on the right track. If you get a yes, ask them if they’d like to chat about how the relationship might come together.
  7. Give them the option of a break. At this point, even if your counterpart likes the idea of working with you, they might need a break. For any of a number of reasons. Maybe they need to chat with some folks on their end, or they need to put an NDA in place. Or, they might just be fatigued. Conversely, they might be reaching for their checkbook and pen. With good feedback in hand, just ask them how they would like to proceed.

One quick note of caution, the reason so many find the next phase (commercialization) to difficult/scary/sleazy is that they’ve not yet done the work required to get there. If you don’t think you know enough to suggest a commercial outcome, you’re right, and you shouldn’t do it yet. There’s nothing wrong with not being ready to close – you just need to stay in the discovery phase until you have what you need.

 Stage Three: Commercialization

As noted above, this phase rattles plenty of folks, but if you’ve put in the work, there’s nothing to fear. I think about it like this:

 Through respectful outreach, you’ve managed to develop a contact.

  1. Within the discovery phase, you learned what you need to know in order to call them a viable prospect.
  2. And, because you’ve worked hard to get consensus, you’ve got their blessing to press on and discuss a commercial structure.

While there’s plenty of work left to do, commercializing a new relationship shouldn’t be feared. Here’s how I like to move forward:

Be clear and make your suggestion: tell your counterpart what you want to do and ask for his/her agreement that it’s the right format.

  1. Ask them if they understand your perspective, and if they have any other questions.
  2. When there are no more questions, ask them what they think about your suggestion(s).
  3. Stop, listen. Breath. Whatever their feedback ends up being, consider it. If it’s positive, move forward. If it’s not, back up, and ask where you slipped. Then, work your way back down the funnel again.
  4. Once you’re confident that you’ve got this dialed in, ask for their commitment to move forward. Don’t worry. If you’ve done your job, this should feel like a natural next step.

That’s all from me, folks. Hope this helps!

Let’s Connect!